課程名稱︰生物有機化學
課程性質︰必修
課程教師︰方俊民
開課學院：
開課系所︰
考試日期（年月日）︰2015/10/20
考試時限（分鐘）：110
試題 :
I.(6%) Describe at least three biological functions of
carbonhydrates, and give at least one example for each function.
II.(9%)The reaction of aldehyde with alcohol forms acetal via an intermediate
of hemiacetal.
Ｏ + +
∥ H H OR' H , R'OH H OR'
╱╲ + R'OH ←→ ╳ ←———→ ╳ + H O
R H R OH R OR' 2
／╲ ＿ ＿
∣ ∣ H ╱ ╲ H ╱ ╲ H
／ ╲╱ ∣ ▕／ ∣ ▕／
HO ∥ ╲ ╱＼ ╲ ╱＼
Ｏ Ｏ OH Ｏ OCH
3
(A) (B) (C)
1. Describe the relationship between the structures of A and B.
2. What is the product for the reaction of compound B with NaBH .
4
3. How will you prepare compound C from compound A?
III.(45%) The molecular formula of glucose is
HOCH CH(OH)CH(OH)CH(OH)CH(OH)CHO, and fructose is
2
HOCH CH(OH)CH(OH)CH(OH)CH(=O)CH OH.
2 2
1. Indicate the position of carbonyl group in glucose.
2. Indicate which carbon containing a primary hydroxyl group in glucose.
3. One can classify fructose as a __(A)__ by the number of carbons, and
as a __(B)__ by its main functional group.
4. What is the product for reaction of glucose with Tollens' reagent?
(AgNO /NH OH)
3 4
5. Draw the structure of D-glucose in Fischer projection.
6. Which carbon certer is responsible for the definition of D-sugar?
7. Does C-3 in D-glucose have R or S configuration?
8. On treatment in aqueous NaOH solution, D-glucose can be converted to
D-fructose via a dienolate ion. Show the reaction mechanism.
9. Draw the cyclic structure of β-D-glucopyranose in chair configuration.
10.β-D-glucopyranose and α-D-glucopyranose are isomers that are specifically
called __(C)__ because they are cyclic stereoisomers having different
configurations at the hemiacetal center.
11.Show the mechanism for the interconversion between β-D-glucopyranose and
α-D-glucopyranose in water.
12.What is the product for reaction of β-D-glucopyranose with
acetic anhydride in the presence of a base pyridine?
13.Draw the cyclic structure of D-fructofuranose.
14.Maltose is a disaccharide Glc(α1→4)Glc formed by two D-glucose molecules.
Draw the structure of maltose.
15.Indicate the acetal and hemiacetal groups in maltose.
IV.(42%)Compounds 1-7 are common L-amino acids.
NH _ NH
ＣOOH HOOC = 2 ／ ╲﹍H = 2
H N┼H ＼／＼ ╲ ／╲ ／＼／＼／＼
2 ＣH COOH N COOH H N COOH
3 | 2
H
(1) (2) (3) (4)
H N ＮH Ｈ
2 ＼∥ Ｎ
∣ NH __╱ ╲ NH Ｎ＿ NH
Ｎ = 2 // \\__// = 2 // \\ = 2
／ ＼／＼／＼ ∣ ∣ ＼／＼ ╲ ╱╲╱╲
H COOH \\__// COOH Ｎ COOH
Ｈ
(5) (6) (7)
1. Draw the zwitterionic form of compound 1.
2. Which compound __(A)__ contains secondary amino group?
3. Which COOH in compound 2 has lower pKa value?
4. Which compound __(B)__ contains the most basic group?
5. Which compound __(C)__ contains a chromophore with absorption at λ =280nm
max
6. Which compound __(D)__ has an imidazole group to act as both general
acid and general base?
7. For compound 1: which group __(E)__ is responsible for pKa1=2.34? which
group __(F)__ is responsible for pKa2=9.69? what is the value __(G)__ of
its isoelectric point (pI)?
8. Which compound __(H)__ has the isoelectric point close to physiological pH?
9. Describe how to separate compounds 1, 2 and 4 by electrophoresis.
10.Draw the structures of two dipeptides contstructed by amino acid
1 and 3.
11.Explain why peptide bond is rather rigid that cannot rotate freely at
room termperature.
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※ 編輯: q510724 (140.112.217.35), 10/21/2015 02:52:28
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